Chief of Staff, Head of Product Strategy – GTM

Role Overview

• Prepare materials and recommendations for executive team and board-level discussions on business unit strategy, including product, pricing, and market expansion.
• Define and maintain executive dashboards, KPI frameworks, and leading indicators to monitor product performance, pricing impact, and GTM effectiveness.
• Support setting the product vision and multiyear roadmap for Auto Integrate, working with executive leadership and Product to align on strategic bets and sequencing.
• Define target customer segments, use cases, and vertical focus; clarify where we win versus competitors and adjacent solutions in fleet, logistics, and broader B2B SaaS.
• In partnership with the product team. ensure market, customer, and competitive insights are translated into clear product requirements, investment cases, and prioritization frameworks.
• Support ownership of the Auto Integrate and payments business model, including 3-year financial plans, scenario analyses, and investment cases for new initiatives.
• Own the quantitative analysis underpinning pricing and packaging decisions for Auto Integrate, using customer cohort data, product usage, and transaction-level patterns to identify opportunities to improve revenue, margin, and adoption.
• Build and maintain robust pricing and monetization models (e.g., unit economics, CLTV, payback, elasticity, sensitivity analyses) that directly inform changes to list pricing, discounting guardrails, value metrics, and packaging constructs.
• Mine product and payments telemetry (e.g., active usage, feature adoption, TPV, invoice/transaction volume, interchange yield) to design and iterate on usage-based and transaction-based monetization levers.
• Create clear, executive-ready pricing and monetization reporting: track and communicate key KPIs (ARPU, attach rate, adoption/activation, gross margin, churn/expansion by price point) and proactively flag risks and opportunities.
• Maintain a source-of-truth pricing and packaging framework, ensuring that analytical logic, assumptions, and metrics are well documented, reproducible, and easy for stakeholders to understand and apply.
• Support product marketing for Auto Integrate, including positioning, messaging, narrative, and sales enablement across self-serve, inside sales, and field motions.
• Partner with Product to ensure launches and roadmap investments are deeply tied to monetization opportunities and measurable business outcomes.
• Own integrated go-to-market plans for major launches and campaigns, partnering with Sales, Marketing, and Partnerships to hit pipeline, activation, and revenue targets.
• Drive adoption and growth programs to increase Auto Integrate participation among existing Fleetio customers and expand usage within current accounts.

Requirements

• 7-10+ years of experience in a network business, B2B SaaS and/or payments across product, product marketing, strategy, or pricing/monetization; with meaningful experience successfully enhancing pricing and GTM decisions for a material product line.
• Proven track record owning product strategy and roadmap for a material product line or business unit, ideally with network or transaction-driven models.
• Deep pricing expertise, including usage-based models, transaction economics, and multiproduct monetization.
• Strong product marketing and GTM experience; able to craft compelling narratives, launch products at scale, and enable sales to win in competitive markets.
• Exceptional analytical and financial acumen, with the ability to build and interpret models, evaluate tradeoffs, and tie product decisions to P&L impact.
• 2+ years experience at a top-tier consulting firm advising on areas of product strategy and pricing preferred.
• Experience in fleet, logistics, mobility, or other “physical economy” verticals is a plus, but not required.
• Entrepreneurial, low ego operating style, comfortable with ambiguity, and excited to run fast in a rapidly scaling business.

Benefits

• Multiple health/dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO
• 4 weeks (increases at year two!)
• 12 company holidays + 2 floating holidays
• Parental leave
• birthing parent (16 weeks paid) non-birthing (4 weeks paid)
• FSA & HSA options
• Short and long term disability (short term 100% paid)
• Community service funds
• Professional development funds
• Wellbeing fund
• $150 quarterly
• Business expense stipend
• $125 quarterly
• Mac laptop + new hire equipment stipend
• Fully stocked kitchen with tons of drinks & snacks (BHM only)
• Remote working friendly since 2012 #LI-REMOTE